Tetrahydrofuran → 3-Ethynyl-1-azabicyclo[2.2.2]octan-3-ol

HRID 900772Notes

Reaction equation

HRID 900772 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][C:2]2=O.C([O-])([O-])=[O:11].[K+].[K+].[CH2:16]1COC[CH2:17]1>>[C:16]([C:3]1([OH:11])[CH:4]2[CH2:7][CH2:8][N:1]([CH2:6][CH2:5]2)[CH2:2]1)#[CH:17]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 5661191-azabicyclo[2.2.2]octan-2-one

Product 1

HCID 36135173-Ethynyl-1-azabicyclo[2.2.2]octan-3-ol

Procedure

Quinuclidinone (76 g, 0.608 mol) was added to a stirred suspension of lithium acetylide ethylene diamine complex (85.7 g, 0.791 mol) in dry THF (500 ml) under nitrogen, at 0° C. After 16 hours at room temperature, a saturated aqueous solution of K2CO3 was added and the mixture was extracted with THF (3 times). Organic phases were combined, dried over MgSO4 and evaporated under vacuum. The white solid was triturated in ether, filtered and dried to give 3-ethynylquinuclidin-3-ol 47 (56.22 g, 61

Workup

  1. extractionthe mixture was extracted with THF (3 times)
  2. dry with materialdried over MgSO4
  3. customevaporated under vacuum
  4. customThe white solid was triturated in ether
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-a101d88a6421485dbd305103ed0f1eca
Source dataset
uspto-grants-2008_04
Patent number
US07361668B2

Reaction notes

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